Tracking vehicular incidents or “drive events” is an important part of fleet management, it allows transportation companies to properly access and manage risks. Typically, onboard vehicle sensors are used to monitor vehicle operation and record drive events. Setting appropriate sensor sensitivities and drive event capturing criteria can help to ensure that valid drive events are captured without capturing invalid non-events, in this way resources are not wasted on storing, transmitting and analyzing non-event data. It is commonly known that different levels of risks are associated with driving in different environments, for example driving downhill may pose a different level of risk than driving on a flat land. However, this is not adequately reflected in the current drive event detection and risk assessment, particularly sensor sensitivity, drive event capturing criteria and risk assessment criteria are not adjusted based on road conditions or drive environments.